Vat dyestuffs and process for making same



United States Patent 9 VAT DYESTUFFS ANSD PROCESS FOR MAKING No Drawing. Application February 9, 1953, Serial No. 335,992

Claims priority, application Germany February 19, 1952 3 Claims. (Cl. 260-276) This invention comprises vat dyestuffs and a making same.

We have found that valuable vat dyestuffs are obtained process for when 2-amino-3,4-phthalyl-acridone, which may contain a halogen atom in the 5-, 6-, 7-, or 8-positions, is condensed in a manner usual for the formation of anthrimides, with l-(3-halogen-benzoy1amino)-anthraquinone which may contain in the 5-position an additional aroylamino group or in the 4,10- or 5,10-positions a pyrimidine ring joined by condensation.

These vat dyestuffs correspond to the general formula (wherein X means a radical of the group consisting of hydrogen, chlorine and bromine, A means an anthraquinonic radical of the group consisting of anthraquinone, 5- benzoylamino-anthraquinone, 4,10- and 5,l-pyrimidineanthraquinone). They dye and print cellulose material clear, yellowish green shades of very good fastness properties.

The following example is given for the purpose of illustrating the invention, the parts being given by weight.

Example A mixture of 400 parts of nitrobenzene, 15 parts of 1-(3-bromo-benzoylamino) -anthraquinone, 10 parts of 2-amino-3,4-phthalyl-acridone, parts of sodium acetate, 0.5 part of copper acetate and 0.5 part of copper powder are heated to 200 C. for 12 hours. After filtering by suction at a moderate temperature, the residue is washed thoroughly at first with nitrobenzene, then with methanol and finally with hot water. The dried, green dyestuif powder corresponds to the formula and dissolves in sulfonic acid with a brown color, and dyes and prints the vegetable fiber to clear, yellowish green shades.

If in this example the 2-amino-3,4-phthalyl-acridone is replaced by 2-amino-6-chloro-3,4-phthalyl-acrid0ne or by 2-amino-7-chlor0-3,4-phthalyl-acridone, dyestuffs are obtained which dye and print to somewhat more yellowish green shades. The use of 1-(3-bromo-benzoylamino)-5- benzoylamino-anthraquinone or of l-(3'-bromo-benzoylamino)-anthrapyrimidine (4,10) instead of l-(3'-bromobenzoylamino)-anthraquinone in the aforesaid condensation results in dyestuffs which dye and print the vegetable fiber to substantially more yellowish green shades than does the dyestuif obtained according to the first paragraph of this example.

We claim:

1. Process which comprises reacting an aminophthalylacridone of the formula wherein X means a radical of the group consisting of hydrogen, chlorine and bromine, with a halogenbenzoylaminoanthraquinone compound of the formula wherein Y means a radical of the group consisting of chlorine and bromine, and A means an anthraquinone radical of the group consisting of anthraquinone and 5-benzoylaminoanthraquinone and wherein the anthraquinone radical is connected to the CONH-group in its l-position, in nitrobenzene as a solvent in the presence of an acid binding agent and of copper to temperatures of 200 C.

3 a a 4 2. Vat dyestufis'of the general formula 3. The vat dyestufi of the formula EN EN 0 O l 0:0 I o f C0-NH 0 o O-NEA l I I wherein X means a radical of the group consisting of hydrogen, chlorine and bromine, A means an anthraquinonic radical of the group consisting of anthraquinone kefernces Cited inthe file 0i this Patent 7 and S-benzoylaminoanthraquinone and wherein the anthraquinone radical is connected to the CONH-group in 20 FOREIGN PATENTS its l-position. 584,819 Great Britain Jan. 23, 1947 

1. PROCESS WHICH COMPRISES REACTING AN AMINOPHTHALYLACRIDONE OF THE FORMULA
 2. VAT DYESTUFFS OF THE GENERAL FORMULA 